We are planning on staying a couple nights at destinations worth checking out. We have set aside two weeks give or take to make the trip and we are aware of the Albermarle Sound. We have also been looking at the Water Way Guide 2023.
OK, great. I made that trip all the way to Elizabeth City, NC a couple years ago. Here are my suggestions from south to north from mid-Florida. I'm skipping south of there and the Okeechobee Waterway for brevity.
St. Augustine. The city marina is right in town. The town and Castillo de San Marcos are an easy walk from the marina. Plan your arrival for slack tide. Changing tides cause strong currents at the marina.
https://www.nps.gov/casa/index.htm
A long day's cruise (78 statute miles) north of there is Plum Orchard Mansion on Cumberland Island. It is a neat place to visit if you have a dinghy and can stand a night at anchor. The Brickhill River anchorage and a dock at which a dinghy can be landed is adjacent to the mansion. NPS volunteer docents live in an apartment at the mansion and give hour-long tours of the mansion three times a day. The mansion had a DC electric system that operated until 1970. The builders of the mansion were friends with Thomas Edison, a proponent of DC electric. A wide, uncrowded beach is a two-mile walk across the island from the mansion. I suggest this place to visit on Cumberland Island because it's five miles north of where the ferries disgorge the tourist hoards and few make it that far from the ferry dock.
https://www.nps.gov/places/plum-orchard.htm
An easy cruise (18 miles) from Cumberland Island in good weather is Jekyll Island. It's worth a stop, especially if you like to bike. The marina has loaner bikes. If the weather is bad or windy, especially against tide, St. Andrews Sound is a fearsome piece of water. There is roundabout way to avoid most of St. Andrews Sound that is ideal for your boat. Your Waterway Guide may have that detailed. If you don't care to stop at Jekyll, continue to Brunswick.
A short cruise north of Jekyll Island is Brunswick, Georgia (16 miles). It will take an Uber or Insta Cart, but that would be good provisioning stop. The city marina is large and well-run with a big cruiser community.
From Brunswick to Savannah is 100 statute miles with some No Wake zones. I split up the trip into two days and anchored. One can make it in a day if one puts the hammer down and pisses off all the fisherman. Savannah is worth a couple-day visit. I have stayed at Hogan's Marina on Turner Creek and Bull River Marina on, well, Bull River. I have friends close to those two spots. Both have significant tidal currents. You'll need an Uber to get into town from both places. There are other marina options that your Waterway Guide may detail.
North of Savannah is Hilton Head and Beaufort, South Carolina. I did not stop at Hilton Head. I did stop at Beaufort, 45 miles. It's a city with a lot of history. There's a marina right downtown. I stayed at Lady's Island Marina across the bridge. I carry my bike with me and rode all over Beaufort. Beaufort, South Carolina is pronounced "Bew-Fort". The Beaufort in North Carolina is pronounced "Bo-Fort".
Next stop is Charleston, 68 miles. I stayed at the Charleston Maritime Center. Your boat will rock constantly from wakes of boats on the nearby river. I survived. The good thing about that marina is it is the base for ferries to Patriot Point and Fort Sumter. The city is an easy walk and there is a grocery nearby for provisioning.
After Charleston is Georgetown, SC. I did not stop there. A few miles north of Georgetown is Wacca Wache Marina (84 miles from Charleston) where I had relatives nearby. Nice place with cheap fuel and a restaurant.
Next is Myrtle Beach (25+/- miles from Wacca Wache, depending on where you stay). I stayed just short of there at Bucksport Plantation Marina to meet friends. It has an adjacent RV park. I do not recommend that place. It worked for a boat and RV to meet and that's all I'll say.
Next stop for me was an anchorage north of Myrtle Beach. From there it was to Southport, North Carolina (50 +/-miles from Myrtle) . I stayed overnight at St. James Marina, ICW MM 314. There's nothing nearby.
North of there, I stayed overnight at Harbor Village Marina (47 miles), ICW MM 267. There's nothing nearby.
North of there, I stayed a couple nights at Oriental Marina in Oriental, North Carolina (87 miles). It was a rough crossing of the Neuse River just before arriving there. Neat little sailing town. A friend met me there. It's a good place to provision.
Next, I stopped at Belhaven, North Carolina (48 miles). I stayed at Dowry Creek Marina, but there are marinas right downtown.
My final stop was Elizabeth City, North Carolina (84 miles). The Albemarle Sound is transited on this leg. On the day I did, it was benign. At Elizabeth City, I actually stayed at Lamb's Marina in Camden a few miles north of Elizabeth City. It's a small, family-run place that has everything you need. There was a restaurant at the marina, but I'm pretty sure it's closed so be provisioned to eat on your boat. There are some free docks at Elizabeth City, but they didn't appeal to me. Only go to Elizabeth City if you intend to cruise the Dismal Swamp Canal on your trip north. If not, take the Virginia Cut and stay at Coinjock Marina. I did not go that way, obviously.
If you are a senior and plan to visit National Parks, one of these is worth the money.
https://www.nps.gov/planyourvisit/senior-pass-changes.htm
To navigate on my Ranger Tug, I carry two iPad Pro 12.9 tablets. I watch Navionics on one and Aqua Maps on the other. They each have their strengths and having two iPads onboard gives me redundancy. I use the Garmin 5212 chartplotter at the helm for radar and sonar. I do not carry paper charts. If having no paper onboard gets you wrapped around the axle, don’t fly on an airliner. There is no paper onboard.
Hopefully someone can take you north of Elizabeth City to the Chesapeake Bay. Have a safe trip.